Boston Holiday 2018 Guide: 12 can't-miss tree lightings, events, and magical moments

Posted by Hannah Davies on


Christmas and holiday things to do in Boston 2018

As a city, we run on Dunkin’, shout “Sweet Caroline” at every Sox game, and are home to some wicked smaht people. Boston is a truly magical place to be any time of year. So naturally, the holiday season brings about a special spirit in Bostonians unlike any other.

Whether you’re a family with young kids or a college student ready to party, Boston's holiday season has something for everyone. Plus, Lovepop HQ calls Boston our home base, so this holiday season, we wanted to add one top priority to your to-do list: FUN! 

Here is our curated list of 12 Things to Do this Holiday Season in Boston:

1. Boston Tree Lightings:

  • Annual Lighting of Columbus Park Trellis (Monday, November 19th at 5 pm)
  • Copley Square Tree Lighting (Monday, November 26th at 5 pm)
  • Massachusetts State House Tree Lighting (Tuesday, November 27th at 5 pm)
  • Faneuil Marketplace: Giant Christmas Tree and Blink! Light Show (Wednesday, November 28th, starts at 2 pm, lights on at 8 pm)
  • Boston Common Holiday Tree Lighting (Thursday, November 29th at 6 pm)

Why: What a better way to celebrate the holiday season than with twinkling lights! Take the chance to explore the city of Boston by attending each of these festive tree lighting celebrations!


2. North End Holiday Stroll
When: Friday, November 30th from 5-10 pm
Where: North End (via Orange Line Haymarket)
Why: Over twenty shops, boutiques, and galleries keep their doors open late and offer discounts for strollers solely for that night. Most locations offer some form of refreshments, and Buon Natale Holiday Stroll participants are encouraged to pick up a “passport” and collect stamps from all the shops for a chance to win prizes.

3. 5th Annual Ugly Sweater Pub Crawl
When: Saturday, December 1st from noon-4pm
Where: Faneuil Hall Registration at Mija Cantina (via Orange Line Haymarket or Green/Blue Line Government Center)
Why: Dig that ugly sweater out of the back of your closet and check out the participating venues with your squad! Thing: Hard Rock, Wild Rover, Sissy K’s, Mija Cantina, Durgin Park, The Hideout, The Point, and more.

4. SantaCon Boston 2018
When: Saturday, December 1st from noon-9pm
Where: Cambridge Route or Boston Route
Why: SantaCon is a FREE to attend pub crawl & mass gathering where people dress in Santa Claus costumes and parade throughout Boston and several other cities around the world. Grab your friends and join in on the festivities!


5. Hanukkah: The Festival of Lights
When: Wednesday, December 5th from 4:30-10 pm
Where: Museum of Fine Arts (via Green Line MFA)
Why: An evening of lively musical performances, engaging tours, art-making, and family-friendly activities. Discover the MFA’s collection of Judaica. View a one-of-a-kind menorah created by local artists Silvina Mizrahi and Sean Clarke, then enjoy a community candle-lighting.

6. 11th Annual Everyone Loves Latkes FREE Tasting Event
When: Saturday, December 9th from 1-2pm
Where: Harvard Square Business Association (via Red Line Harvard Square)
31 Brattle Street
Cambridge, MA 02138
Why: Hot and delicious potato pancakes will be sampled between 1:00 pm and 2:00 pm on Brattle Plaza, in front of Brattle Florist (31 Brattle Street)

7. Jingle Bell Run/Walk
When: Saturday, December 9th
Registration at 8 am
5K starts at 9 am
Where: Boston Common at the corner of Beacon Street and Charles Street
Why: The Arthritis Foundation’s original Jingle Bell Run is a fun way to get decked out and be festive while racing to raise funds and awareness. Put on your favorite holiday costume. Tie jingle bells to your shoelaces. ’Tis the season to live it up and be jolly for a reason!

8. Yulefest 5k
When: Saturday, December 9th at 9:30 am
Where: Harvard Square (via Red Line Harvard Square)
42 Church Street, Cambridge
Why: Grab your friends and get your yule on! Registration includes a cozy Yulefest knit hat plus access to a festive block party featuring DJ Renselect & MC Vyper.

Lovepop Gingerbread House pop up card

9. Gingerbread Houses for Grown-Ups
When: December 11th from 7-10 pm
Where: Fairmont Copley Plaza Hotel (via Green Line Copley)
138 St. James Avenue
Why: Do you miss building gingerbread houses from when you were a kid? Join the Fairmont Copley Plaza Hotel for an adult evening of decadently sweet construction and cocktails.

10. BeerAdvocate’s IPA Fest
When: Saturday, December 15th from noon - 10 pm
Where: Black Falcon Cruiseport Boston, 1 Black Falcon Ave (Seaport)
Why: Sponsored by Dogfish Head Craft Brewery, this one day, two session event will be held at the Flynn Cruiseport Boston, and will explore and celebrate the tremendous diversity of a beer category that continues to attract more fans year after year: India Pale Ales. Each of the 150+ beers from 40+ breweries in attendance will be an India Pale Ale (plus a few India Pale Lagers for good measure).

11. CraftBoston Holiday
When: Saturday, December 15th - Monday, December 17th from 11am-5pm
Where: Hynes Convention Center (via Green Line Hynes Convention Center)
Why: Guests can meet and interact with the artists who make handmade goods using centuries-old skills in mediums like ceramics, fiber, glass, metal, and wood. A ticket to CraftBoston Holiday supports its presenter, Society of Arts + Crafts, the nation's oldest craft nonprofit.



12. First Night Boston 2019
When: Monday, December 31st at noon - Tuesday, January 1st
Where: Copley Square/Back Bay (via Green Line Copley or Orange Line Back Bay)
Why: Entertainment and special attractions will be focused in Copley Square and Back Bay. Many of the beloved traditions of First Night’s past will continue, including cultural and musical performances in various indoor venues around the Back Bay, fantastic ice sculptures, light displays, the People’s Procession at 6:00 PM, and 7:00 PM Family Fireworks sponsored by The Mugar Foundation on Boston Common.

And for any holiday festivities, you can always make a magical moment even more unforgettable with Lovepop. Visit our retail locations across Boston or pick a favorite online with our new holiday collection.

Shop Lovepop Holiday Cards 


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